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Toby Keith: Remembering the Legend

Toby Keith: Remembering the Legend

Toby Keith: Remembering the Legend

Don Chase Remembers the Life and Career of Toby Keith

Author Don Chase
Superstar Toby Keith and fellow Country star Carrie Underwood in Nashville, Tennessee. (Photo by Erika Goldring/Getty Images for BMI)

By now you are probably aware that the world of Country music lost a superstar last night. At the young age of 62, Toby Keith lost his battle with stomach cancer. Toby was surrounded by his family and friends.

I was sitting here in The BIG 95.7 WKML studio around 4:00 this morning when I heard this sad news and I have to confess, I was not ready.

The first time I met Toby was in 1997 at the annual Country Radio Seminar in Nashville, Tennessee.

One funny story that I remember from that event was that by chance, a friend who was a major record label representative introduced me to Toby. After the three of us had talked for a few minutes, Toby’s record rep said, I hear that LeAnn Rimes is somewhere in the room. Toby responded, “who the hell is LeAnn Rimes?” We all had a big laugh until we realized LeAnn was standing directly behind Toby waiting on her chance to meet the superstar. At the time, LeAnn was doing really well with her new song “Blue.” I think she was only 13 years old at the time.

Personally, I will always look back and find it puzzling that Toby never played Fort Liberty’s 4th of July Celebration. I’m not sure why. What I do know is that a new attendance record would have been set if Toby could have performed. I so respected Toby for supporting those in uniform during his career.

If you were to ask me about my favorite Toby Keith song, it would take me a moment. First, I would go back to 1993 and Toby’s first song “Should’ve Been a Cowboy” which was a monster hit on The BIG 957. It was Toby’s first number one song and if I remember correctly, it was the most played Country song between 1990 and 1999.

My personal list of Toby Keith favorites would include “My List,” a great tune that reminded all of us to focus on what’s most important in our lives. “As Good As I Once Was,” the story of a bunch of guys hanging out at a local bar and unbelievably a fight breaks out was a great one. “Courtesy of The Red, White, and Blue (The Angry American)” which was inspired by the sad attack on America on September 11th and of course, “How Do You Like Me Now” would also make the list.

In the end, I hope Toby could feel that millions of fans were praying that he could win his battle. To Toby’s wife Tricia and their children Shelley, Krystal and Stelen, prayers continue for you.

Toby, thank you for all you did for Country radio!

Don Chase is living out his dreams, anchoring The Big Wake-Up with Don Chase & Sarah weekday mornings on KML. With over 35 years with Beasley Media, Don believes that the best is yet to come. The unofficial Mayor of Fayetteville radio, Don Chase writes about Fayetteville and North Carolina news, as well as entertaining perspectives on music, culture and more.

Five of Toby Keith's Songs That Will Live Forever

Toby Keith’s passing at the age of 62 last night (2/5) has hit the country music community hard. The Country Music Hall of Fame said, “Toby Keith was big, brash, and never bowed down or slowed down for anyone. He wrote his breakthrough songs and later formed his own record label when he felt underserved by Nashville. For three decades, he reflected the defiant strength of the country music audience. His memory will continue to stand tall.”

In October, before his death, Keith took to Instagram to reveal that he would play two shows in Las Vegas in December.  In a video clip posted to Instagram, Toby said, “Hi everybody, this is Toby Keith. It’s been a while. You know what I’ve been doing, been on the old roller coaster, but Almighty is riding shotgun. He’s letting me drive for some reason. I’m making a big announcement. I’m doing a little deal, and I would start with Great Las Vegas at the MGM at Dolby Live at the park at MGM on December 10 and 11; you can do the National Finals Rodeo and the show if you want to. I was gonna sit around here and do nothing like I have been or get up and go outside and not let the old man in, you know what I mean?” Sadly, that

He added in part, “The old devil has been after me a little bit, but I have him by the horns right now. So instead of just sitting around and waiting, we’re gonna get the band back together, so come on out, hang out at the rodeo, and watch the show. We’re gonna have a blast. Get it all going again, big dog daddy style. Should have been a cowboy; go to the rodeo. See ya.”

Those Vegas shows, which played through January (2024), were his last shows on stage playing for fans.

Blake Shelton presented his fellow Oklahoman with the “Country Icon Award” at the September inaugural People’s Choice Country Awards (2023).

Early in his career, almost 20 years ago (2004), Blake toured and opened shows for Toby Keith nationwide. At the time, he told me, “Toby is one of those guys that is so famous and so big, and he is one of those artists that’s just worldwide. You don’t have to be a country music fan to be a Toby Keith fan. It’s just way bigger than that. I step on stage with over 20 thousand people per night, and 15,000 of them may or may not have ever heard of me. Touring with Toby has probably been the biggest break I’ve had since I started doing this.”

As the world shines a light on Toby Keith and his music today (2/6) with his passing, we shine a light on five of his greatest songs.

RELATED: Carrie Underwood, Jelly Roll and More React To Toby Keith’s Death

  • "Should've Been a Cowboy" (1993)

    This is his debut single and the song people will always associate with Toby. Many artists mentioned the song and its lyrics in their tribute to him after his death (2/6). Keith wrote the song himself, and it has always been his anthem. The song has received more than three million spins on country radio, making it the most-played country song of the 1990s. Over the years, the song has been a staple following sporting events at Oklahoma State University (home of the Cowboys), often played over the venue’s PA system several times in succession as fans emptied the stadium or arena.

  • "How Do You Like Me Now?!" (1999)

    This song brought Keith to superstardom. Toby told me the inspiration for the song in 2000. “Initially, I said, ‘Here’s my title: ‘You Never Loved Me Before, So How Do You Like Me Now?’ It’s one of my catchphrases. A lot of people become successful after they’ve been told they won’t ever be so that people can relate to this. It can be about an old flame or a boss or a teacher -whatever it means to each individual. It was a fun song to write.”

  • "I Wanna Talk About Me" (2001)

    This is another fun song and a big hit for Keith. The song was originally pitched to Blake Shelton, whose label turned it down. After recording the song, Keith said he knew he would get banged around for the song a bit. He noted, “They’re going to call it a rap, [although] there ain’t nobody doing rap who would call it a rap.”

    The music video for the song shows Toby in many different situations, including a man shopping with his girlfriend or wife, a police officer, a motorcycle rider, and a surgeon.

  • "Courtesy of the Red, White, and Blue (The Angry American)" (2002)

    The song he wrote after the 9/11 attacks on America and was also inspired by Keith’s father’s death in March 2001. In a November 2003 interview with CBS, Keith said of writing the song: “I was so angry when we were attacked here on American soil that it leaked out of me.”

    The music video for the song features Toby performing the song, playing a red, white, and blue guitar, and showing images of his own father fighting in a war.

  • "Red Solo Cup" (2011)

    Keith sure is good at fun party songs, and he proved it once again with this song, which was the only song on the album Clancy’s Tavern that he did not write. The song was written by the Warren Brothers in Nashville.

    The music video includes cameos from Jeff Dunham (and his character Bubba J), Carrot Top, Ted Nugent, Sammy Hagar, Craig Ferguson, Geoff Peterson, Roger Clemens, Eric Church, Joe Nichols, Lance Burton, and Larry Bird, among others.

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